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Windsor

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Windsor Flights as Low as $419

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Tue, Nov 17 - Wed, Dec 2
MIA
Miami Intl.
LEB
Lebanon Municipal
$419 Roundtrip, found 2 days ago
$419
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Nov 17 from Miami Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $419 found 2 days ago
Delta
Wed, Nov 18 - Wed, Dec 2
MIA
Miami Intl.
LEB
Lebanon Municipal
$429 Roundtrip, found 2 days ago
$429
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $429 found 2 days ago
Delta
Wed, Nov 18 - Tue, Dec 1
MIA
Miami Intl.
LEB
Lebanon Municipal
$440 Roundtrip, found 2 days ago
$440
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $440 found 2 days ago
Delta
Wed, Nov 18 - Fri, Dec 4
MIA
Miami Intl.
LEB
Lebanon Municipal
$450 Roundtrip, found 2 days ago
$450
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Fri, Dec 4, priced at $450 found 2 days ago
American Airlines
Wed, Nov 18 - Thu, Dec 3
MIA
Miami Intl.
LEB
Lebanon Municipal
$470 Roundtrip, found 2 days ago
$470
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Thu, Dec 3, priced at $470 found 2 days ago
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$474 Roundtrip, found 10 hours ago
$474
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $474 found 10 hours ago
Delta
Tue, Nov 17 - Thu, Dec 3
MIA
Miami Intl.
LEB
Lebanon Municipal
$479 Roundtrip, found 2 days ago
$479
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Nov 17 from Miami Intl. to Lebanon Municipal, returning Thu, Dec 3, priced at $479 found 2 days ago
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$484 Roundtrip, found 10 hours ago
$484
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $484 found 10 hours ago
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$495 Roundtrip, found 2 days ago
$495
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $495 found 2 days ago
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$495 Roundtrip, found 10 hours ago
$495
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $495 found 10 hours ago
Delta
Mon, Nov 16 - Wed, Dec 2
MIA
Miami Intl.
LEB
Lebanon Municipal
$500 Roundtrip, found 2 days ago
$500
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Nov 16 from Miami Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $500 found 2 days ago
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$505 Roundtrip, found 2 days ago
$505
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $505 found 2 days ago
United
Tue, Nov 17 - Wed, Dec 2
MIA
Miami Intl.
LEB
Lebanon Municipal
$506 Roundtrip, found 10 hours ago
$506
Roundtrip
found 10 hours ago
Select United flight, departing Tue, Nov 17 from Miami Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $506 found 10 hours ago
Delta
Wed, Nov 18 - Mon, Nov 30
MIA
Miami Intl.
LEB
Lebanon Municipal
$510 Roundtrip, found 2 days ago
$510
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Mon, Nov 30, priced at $510 found 2 days ago
United
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$511 Roundtrip, found 10 hours ago
$511
Roundtrip
found 10 hours ago
Select United flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $511 found 10 hours ago
American Airlines
Sat, Dec 12 - Mon, Dec 21
OKC
Will Rogers World
LEB
Lebanon Municipal
$598 Roundtrip, found 16 hours ago
$598
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Sat, Dec 12 from Will Rogers World to Lebanon Municipal, returning Mon, Dec 21, priced at $598 found 16 hours ago

Cheap Flights to Windsor

Fall in love at first flight with your vacation to Windsor by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Windsor on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Windsor, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Windsor

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windsor with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the VSF airport.

What is the cheapest month to fly to Windsor?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Windsor are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windsor?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Windsor.

What airport is best to fly into Windsor?

When you’re planning your trip to Windsor, convenience is the name of the game. Luckily, Windsor Lebanon Municipal Airport is nearby so you can deplane and get going on checking off everything on your Windsor must-do list.

How much are flights to Windsor?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windsor on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $419, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Windsor?

The trick to saving a stack of cash on your flight to Windsor? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $419 right now, why wait?

Windsor Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$419

Last Minute Hotel Deals in Windsor

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3 out of 5
122 Best Rd Windsor VT
Stay at this cabin in Windsor. Enjoy free WiFi, free parking, and a garden. Popular attractions Hartland Public Library and Path of Life Garden are located ...
9.8/10 Exceptional! (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views!"

Reviewed on Jan 5, 2026

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Fat Sheep Farm & Cabins
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road West Lebanon NH
Book a stay at this business-friendly hotel in West Lebanon. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the pool in ...
8.4/10 Very Good! (1,007 reviews)
"The staff was just ok here. They weren't rude by any means but they weren't super friendly either. Th I s hotel is old and rustic and has nit had any updates done. The bedding did not seem clean and the bathroom needed a new shower curtain, which was ripped up at the bottom and dirty. We were supposed ..."

Reviewed on Oct 8, 2026

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Fireside Inn & Suites West Lebanon
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,008 reviews)
"It is a old building which is why the floors creak. No AC but able to open the windows to let the cool mountain air in. Bathroom has a musty smell."

Reviewed on Oct 9, 2026

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The Mountain Inn at Killington
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive White River Junction VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
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White River Inn and Suites
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (1,380 reviews)
"Room was good size and bathroom area was adequate for two people. There was some audible road noise. Breakfast was ok with cold breakfast sandwiches that could be heated up in the microwave."

Reviewed on Oct 9, 2026

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Align Inn Vermont
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (615 reviews)
"Lovely feel to the hotel with friendly staff. Room was comfortable and location is excellent. Love Woodstock as a destination. I am never the biggest fan of breakfast, but really enjoyed it for once"

Reviewed on Oct 7, 2026

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Woodstock Inn & Resort
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in ...
8.6/10 Excellent! (918 reviews)
"The staff is amazing here at Jackson Gore Village. There were actually some issues with our stay and we reported to the front desk. The staff was really helpful and took care of the issue immediately. Katie, the manager, followed up the next day and further resolved the issue. The way they treat ..."

Reviewed on Oct 9, 2026

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Jackson Gore Village, A Vail Resorts Property
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 out of 5
285 Thundering Brook Road Killington VT
Book a stay at this family-friendly hotel in Killington. Enjoy free breakfast, a sauna, and a 24-hour front desk. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (321 reviews)
"We reserved a room that stated it was 344 sq ft..All the pics showed 2 chairs and larger. We were given a room on first floor number 208 in the farm house. The room was around 132 sq ft. There was one chair. We could barely move. The entrance was not 3 ft wide. The room was 80 degrees. Heat is connected ..."

Reviewed on Oct 8, 2026

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Mountain Meadows Lodge
See all 2,714 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.